In 1999, Molly McConnell walked into the Grand Avenue Boxing Gym in Portland, Oregon for the first time, and her love affair with the sport of boxing began.

After a few weeks of participation in a women's boxing fitness program, Molly was approached by coach Ron Woodward and invited to train with him to compete as an amateur boxer. Molly was an eager student and a quick study, and within a couple of months she competed in her first amateur bout. Within a year, Woodward had led Molly to several state championship titles, including both the Oregon and Washington State Golden Gloves. Molly's great potential and hard punching style led Woodward to urge her to begin training with Bill Meartz at the West Portland Boxing Gym. Meartz has worked with countless national champions and US Olympians and is regarded as one of the best amateur boxing coaches in the country.

In 2001, Molly began her studies with Meartz and her amateur career took off. She quickly earned a reputation for her piston like jab and her impressive power in both hands. Under Meartz's expert guidance, Molly went on to win four amateur national championship titles. She took a bronze medal at the 2002 National PAL Championships and won the Women's National Golden Gloves, becoming the first person from Oregon (male or female) to take home a national golden gloves championship in 18 years. She also won the Ringside World Championship Tournament, scoring three stoppages in her four fights. In 2003, Molly took a silver medal at the US Women's Championships in a fight that was decided by one point. She also took a silver medal at the National Golden Gloves in a highly controversial decision. She went on to win the National PAL Championship and repeated as the champ at the Ringside World Tournament. She ended 2003 as the number one ranked amateur welterweight in the country.